Sodium hydride → HCID 13526446, compound

Participants

Reaction Steps

To a stirred suspension of 6.14 g. of sodium hydride [50% dispersion in oil, (0.128 mole)] in 150 ml. of tetrahydrofuran (distilled from lithium aluminum hydride) at 0° C. under nitrogen was added 10.0 g. (0.0256 mole) of 5,6-bis(p-hydroxyphenyl)-2,3-dihydroimidazo[2,1-b]thiazole hydrobromide. After 30 minutes, 17.82 g. (0.0768 mole) of 2,2,2-trifluoroethyl trifluoromethanesulfonate was added dropwise, maintaining the temperature below 0° C. After stirring overnight at room temperature, the suspension was added portionwise to 500 ml. of ice water under nitrogen and extracted three times with methylene chloride. The organic layer was washed with water, dried over potassium carbonate and concentrated in vacuo. The residue was recrystallized from methylene chloride-hexane to give 5,6-bis[p-(2,2,2-trifluoroethoxy)phenyl]-2,3-dihydroimidazo[2,1-b]thiazole, m.p. 163°-164° C.

Provenance & Evidence